HCID 23047401, compound → HCID 23047448, compound

HRID 2107083Notes

Reaction equation

HRID 2107083 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][N:6]2[C:15]=1[CH:16]([CH3:18])[CH3:17]>[O-2].[O-2].[Mn+4].C(OCC)C>[CH:16]([C:15]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[C:4]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:3]=1[CH:2]=[O:1])=[CH:13][CH:12]=[CH:11][CH:10]=3)([CH3:18])[CH3:17]

Participants

4

Reactant 1

HCID 23047401HCID 23047401, compound

Product 1

HCID 23047448HCID 23047448, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-hydroxymethyl--3-isopropyl-1phenylpyrrolo-[2,1-a]isoquinoline (2.05 g), activated manganese dioxide (22.56 g) and diethyl ether (120 ml) was stirred at the ambient temperature under an atmosphere of argon for 16 hours. The suspension was then filtered, the filtrate was evaporated and the resulting residue was subjected to flash chromatography on silica gel, using as eluent a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (3:1 v/v), to give 3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinoline-2-carboxaldehyde (1.3 g) in the form of a yellow solid, m.p. 134°-136° C. [N.M.R. (in CDCl3): 1.54 (6H, d, J=7 Hz), 4.30 (1H, septet, J=7 Hz), 6.82 (1H, d, J=8 Hz), 7.06-7.54 (9H, m), 7.89 (1H, d, J=8 Hz) and 9.76 (1H, s); Mass spectrum (electron impact) m/e=313].

Workup

  1. filtrationThe suspension was then filtered
  2. customthe filtrate was evaporated
  3. additiona mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (3:1 v/v)

Sources & evidence

ORD record
ord-613a0ec34e9140d3b9e0ab1388d459ec
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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